Bill Henderson knew he had accomplished something as a jazz singer when he first played New York in 1958. He was at the Village Vanguard, the most famous club in jazz’s most famous city, and on a bill with the popular combo the Three Sounds and the man who was both then and now the most celebrated saxophonist in all of jazz: Sonny Rollins.

“I was in the middle of a ballad, and I heard something moving in back of me on the bandstand,” he told me last weekend. “I realized that Sonny was playing behind me! We hadn’t planned that or rehearsed anything; he just did that spontaneously. After we finished, he said ‘It just seemed like you guys were having so much fun that I wanted to get in on it.'”

“In a way, it was like Sonny was giving me a kind of sanction,” Mr. Henderson said.

Mr. Henderson would realize, however, that there’s a difference between gaining the approval of the cognoscenti and getting the chance to show the public what you can do. One of the great male jazz singers of all time, Mr. Henderson has only made about a half dozen appearances and performed in New York only on a handful of occasions. His run at Jazz at Lincoln Center’s Allen Room, which began last night, marks the first time he’s headlined a show in New York in more than 20 years.

Mr. Henderson could be classified as a blues singer, a jazz stylist, and a pop crooner. Like Sarah Vaughan, he incorporates the mechanics of note production into his music; like Tony Bennett, he beautifully employs the sound of strain. Born in Chicago (he admits to 1926), Mr. Henderson said he learned his singing style from his father, a chemist: “He used to sing ‘There’s Danger in Your Eyes, Cherie’ to my mother all the time.”

Mr. Henderson got his first job after he won a contest given by famous vaudevillian Phil Baker at the Chicago Opera House. A singing-dancing toddler, he was given the privilege of changing into his sailor suit with the chorus girls. “I was the envy of everybody, but I was too young to understand why,” he said.

Mr. Henderson spent the early 1950s touring Europe as part of a U.S. Army Special services package, which also included the famous singer Vic Damone. After returning home to Chicago, Mr. Henderson worked most often with old friend pianist Ramsey Lewis and Lewis’s trio, then hit New York in 1958.

“All these people told me that I should call them if I ever got to Manhattan,” he said. “I did, but the only one who responded was Billy Taylor. He introduced me to all the jazz record producers.”

Mr. Henderson did sessions for both Riverside (with Cannonball Adderley) and Blue Note (with Horace Silver),but he didn’t make a full album until he was back in Chicago. “Bill Henderson with the Ramsey Lewis Trio” is now part of a two-CD package called “The Complete Vee-Jay Recordings,” on Koch Jazz. From that time on, Mr. Henderson worked with some of the greatest musicians and bands around.

His single greatest album, “Bill Henderson With the Oscar Peterson Trio,” was the result of his traveling with the great pianist as a special guest vocalist. Unfortunately, he didn’t get to make a record with Art Blakey and the Jazz Messengers when he toured Japan with that group (although tapes exist). Mr. Henderson also hit the road for several years with Count Basie.

“Basie kept trying to get me to do some of Joe Williams’s specialties, but I had my own book of great arrangements by Ernie Wilkins, Benny Golson, and Thad Jones.” He sings “Yesterday” on one of the band’s more eclectic album projects, “Basie’s Beatle Bag.”

Mr. Henderson spent the 1960s as a traveling jazz singer, and the 1970s and 1980s as a working actor in Hollywood. His first acting job came as the result of his friendship with Bill Cosby. His best-remembered appearance was as a doctor in the 1991 “City Slickers,” and his most recent was playing a transvestite named Tinkerbelle 14 months ago in the ongoing CBS series “Cold Case Files.”

Mr. Henderson has made considerably more money acting than singing. Yet there’s no doubt the world of jazz and standards has been more rewarding. He told me that, when he ran into the great songwriter-singer Johnny Mercer, Mercer said: “They tell me you sound like me – but you sound better!” Now New Yorkers have a rare opportunity to hear him in action.

Until January 22 (Allen Room, Lincoln Center, 22-721-6500).